Tributylvinyltin → HCID 90449481, compound

HRID 1411307Notes

Reaction equation

HRID 1411307 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11]3)[CH2:9][N:8]([C:22]([O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])=[O:23])[C:5]2=[CH:6][CH:7]=1.[CH2:31]([Sn](CCCC)(CCCC)C=C)[CH2:32]CC.[Cl-].[Li+]>O1CCCC1>[CH:31]([C:2]1[CH:3]=[C:4]2[C:10]3([CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11]3)[CH2:9][N:8]([C:22]([O:24][CH2:25][CH2:26][Si:27]([CH3:29])([CH3:28])[CH3:30])=[O:23])[C:5]2=[CH:6][CH:7]=1)=[CH2:32]

Participants

5

Reactant 3

HCID 81998TributylvinyltinHCID 433294Lithium ChlorideHCID 90449581HCID 90449581, compound

Product 1

HCID 90449481HCID 90449481, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The 1-(2-(trimethylsilyl)ethyl) 1′-tert-butyl 5-bromospiro[indoline-3,3′-pyrrolidine]-1,1′-dicarboxylate (1.00 g, 2.01 mmol) obtained in Step 2 of Example 383 was dissolved in tetrahydrofuran (20 mL). Thereafter, tributyl(vinyl)tin (1.40 mL, 4.79 mmol), tetrakistriphenylphosphine palladium (240 mg, 0.21 mmol), and lithium chloride (260 mg, 6.13 mmol) were added to the above obtained solution at room temperature, and the thus obtained mixture was then stirred for 21 hours while heating under reflux. Thereafter, the reaction solution was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain 1-(2-(trimethylsilyl)ethyl) 1′-tert-butyl 5-vinylspiro[indoline-3,3′-pyrrolidine]-1,1′-dicarboxylate (723 mg, 81%) in the form of a light yellow solid.

Workup

  1. temperaturewhile heating
  2. temperatureunder reflux
  3. customThereafter, the reaction solution was purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-9dcfa22cf61b40bf9b2b26da4f617735
Source dataset
uspto-grants-2014_12
Patent number
US08921576B2

Reaction notes

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